Emerging trends in the re-inhabitation of central cities and government funding of numerous financial incentives have succeeded in making brownfield redevelopment a far more lucrative opportunity for developers over the past decade. However, the redevelopment process itself remains virtually unchanged, maintaining a narrow focus on environmental remediation, site engineering, and short-term market demand. Land use, instead of design, drives the entire process. This approach fails to sustain development and recognize larger redevelopment opportunities based on local and regional context. Despite an increasing amount of public money used to fund incentives, development continues to overlook potential positive externalities presumably to avert risk and increase feasibility. The purpose of this thesis is to re-examine brownfield redevelopment from the perspective of urban design in order to define ways in which design might offer solutions to these shortcomings and play a more critical role in future redevelopments. Using case studies of past redevelopments of former auto plant sites, Landscape Urbanism in brownfield redevelopment, and design proposals for auto plant sites from the GM and Ford closings of 2005-2006, the thesis investigates three primary questions. First, what is the conventional brownfield redevelopment process, to what extent has urban design been involved, and what are the major issues and lessons that can be learned? Secondly, what examples of brownfield redevelopment have integrated urban design to addresses these issues and what are the specific principles that inform design? Finally, how can urban design strategies, based on principles of Landscape Urbanism, lead the redevelopment of brownfield sites?